Haloperidol

Iupac Name：4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one

CAS No.: 52-86-8

Molecular Weight：375.868

Modify Date.: 2022-03-31 20:13

Introduction: Haloperidol is one of the most actively used modern neuroleptics. Its high antipsychoticactivity is combined with a moderate sedative effect. It effectively stops various types ofpsychomotor excitement. It is used for schizophrenic psychoses, manic, paranoid, anddelirious conditions, depression, psychomotor excitement of various origins, and for delirium and hallucinations of different origin. View more+

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1. Names and Identifiers

1.1 Name: Haloperidol
1.2 Synonyms: 1-Butanone, 4-[4- (4-chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)- 1-Butanone, 4-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)- 4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanon 4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone 4-(4-(para-Chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone 4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-4’-fluoro-butyrophenon 4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-4’-fluorobutyrophenone 4-(4-(p-Chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone 4-(4-hydroxy-4’-chloro-4-phenylpiperidino)-4’-fluorbutyrophenone 4-(4-hydroxy-4’-chloro-4-phenylpiperidino)-4’-fluorobutyrophenone 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-bu 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one 4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone 4-[4-(4-Chlorphenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorphenyl)butan-1-on 4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone ALDO Aloperidin Bioperidolo Brotopon Butyrophenone, 4-[4- (p-chlorophenyl)-4-hydroxypiperidino]-4'-fluoro- Dozic Einalon Einalon S EINECS 200-155-6 Eukystol Haldol haldol Decanoate Halol Haloperidol [USAN:BAN:INN:JAN] Halosten Keselan Linton MFCD00051423 Peluces Pernox r1625 Serenace Sernas Sernel Sigaperidol

1.3 CAS No.: 52-86-8

1.4 CID: 3559

1.5 EINECS(EC#): 200-155-6; 612-377-4

1.6 Molecular Formula: C21H23ClFNO2 (isomer)

1.7 Inchi: InChI=1S/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2

1.8 InChkey: LNEPOXFFQSENCJ-UHFFFAOYSA-N

1.9 Canonical Smiles: C1CN(CCC1(C2=CC=C(C=C2)Cl)O)CCCC(=O)C3=CC=C(C=C3)F

1.10 Isomers Smiles: C1CN(CCC1(C2=CC=C(C=C2)Cl)O)CCCC(=O)C3=CC=C(C=C3)F

2. Properties

3.1 Density: 1.3 (20 C)

3.1 Melting point: 152 °C

3.1 Boiling point: 529

3.1 Refractive index: 1.581

3.1 Flash Point: 274

3.1 Vapour pressure: 4.8X10-11 mm Hg @ 25 deg C /Estimated/

3.1 Precise Quality: 375.14000

3.1 PSA: 40.54000

3.1 logP: 4.36350

3.1 Solubility: 2.058mg/L(22.5 ºC)

3.2 AnalyticLaboratory Methods: HALOPERIDOL; IS EXTRACTED FROM ALKALINE SOLN OF SAMPLE OF CHLOROFORM;. CHLOROFORM; EXTRACT IS CONCN & ALIQUOT IS ANALYZED BY GAS CHROMATOGRAPHY.

3.3 Appearance: Clear, colorless solution with no odor.

3.4 Storage: Keep Cold.

3.5 Chemical Properties: White Crystalline Powder

3.6 Color/Form: white

3.7 Physical: Solid

3.8 pKa: 8.3(at 25℃)

3.9 Water Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.39?mg/mL

3.10 Spectral Properties: UV max (9:1 0.1M HCl:methanol): 247,221 nm (Epsilon: 13300, 15000)
Intense mass spectral peaks: 123 m/z, 189 m/z, 224 m/z, 237 m/z, 375 m/z
MASS: 42411 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
UV: 2315 (Absorption Spectra in the UV and Visible Region, Academic Press, NY)

3.11 Stability: Stable at normal temperature and pressure.

3.12 StorageTemp: 2-8°C

3. Use and Manufacturing

4.1 Definition: ChEBI: A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.

4.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 86 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 2 of 86 companies. For more detailed information, please visit ECHA C&L website

Of the 8 notification(s) provided by 84 of 86 companies with hazard statement code(s):

H301 (98.81%): Toxic if swallowed [Danger Acute toxicity, oral]
H315 (90.48%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (84.52%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (90.48%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (86.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H361 (86.9%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P261, P264, P270, P271, P272, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501

4.3 Methods of Manufacturing: /CONDENSATION OF/ 4-(P-CHLOROPHENYL)-4-PIPERIDINOL; ... WITH 4-CHLORO-4'-FLUOROBUTYROPHENONE; BY HEATING TOLUENE; SOLN OF REACTANTS IN PRESENCE OF SUITABLE CONDENSING AGENT. ... ISOLATION FROM REACTION MIXTURE & RECRYSTALLIZATION FROM SUITABLE SOLVENT ... (DIISOPROPYL ETHER;).

4.4 Usage: Haloperidol is one of the most actively used modern neuroleptics. Its high antipsychoticactivity is combined with a moderate sedative effect. It effectively stops various types ofpsychomotor excitement. It is used for schizophrenic psychoses, manic, paranoid, anddelirious conditions, depression, psychomotor excitement of various origins, and for delirium and hallucinations of different origin.

4. Safety and Handling

5.1 Symbol: GHS06, GHS08

5.1 Hazard Codes: T

5.1 Signal Word: Danger

5.1 Risk Statements: R60;R61;R25;R36/37/38;R43

5.1 Safety Statements: S53;S26;S36/37/39;S45

5.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl haloperidol, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

5.2 Packing Group: III

5.2 Octanol/Water Partition Coefficient: log Kow = 4.30

5.3 Hazard Class: 6.1(b)

5.3 Hazard Declaration: H301-H315-H317-H319-H335-H361

5.3 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

5.4 RIDADR: UN 2811

5.4 Caution Statement: P261-P280-P301 + P310-P305 + P351 + P338

5.4 Formulations/Preparations: Oral tablet - 0.5, 1, 2, 5, 10, 20 mg, Haldol (scored), (Ortho-McNeil)
Haloperidol Decanoate: Parenteral: Injection for IM use only: 50, 100 mg (haloperidol) per mL, Haldol Decanoate (with benzyl alcohol 1.2% in sesame oil), (Ortho-McNeil), also promoted by Scios Nova), Haloperidol Decanoate Injection (with benzyl alcohol 1.2% in sesame oil), (American Pharmaceutical Partners, Apotex, Bedford, GensiaSicor). /Haloperidol decanoate/
Haloperidol Lactate: Oral solution: 2 mg (haloperidol) per mL, Haldol Concentrate (with methylparaben), (Ortho-McNeil), Haloperidol Intensol (with parabens and propylene glycol), (Roxane). Parenteral injection: 5 mg (haloperidol) per mL, Haldol (with parabens), (Ortho-McNeil). /Haloperidol lactate/

5.5 WGK Germany: 3

5.5 RTECS: EU1575000

5.5 Toxicity: LD50 orally in rats: 165 mg/kg (Goldenthal); i.p. in mice: 60 mg/kg (Collins, Horlington)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Skin irritation, Category 2

Skin sensitization, Category 1

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed H315 Causes skin irritation H317 May cause an allergic skin reaction H319 Causes serious eye irritation H335 May cause respiratory irritation H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P271 Use only outdoors or in a well-ventilated area. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in DMSO-d6

1H NMR : 400 MHz in DMSO-d6

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

52-86-8Total: 6 Synthesis Route

462-06-6 128 Suppliers

52-86-8 147 Suppliers

Literatures:
Janssen et al. Journal of Medicinal and Pharmaceutical Chemistry, 1959 , vol. 1, p. 281,284
Yield: null

103-84-4 133 Suppliers

52-86-8 147 Suppliers

Literatures:
Hashizume, Kazunari; Hashimoto, Naoto; Miyake, Yoshihiro Bulletin of the Chemical Society of Japan, 1997 , vol. 70, # 3 p. 681 - 687
Yield: null

91335-13-6 1 Suppliers

52-86-8 147 Suppliers

Literatures:
Janssen et al. Journal of Medicinal and Pharmaceutical Chemistry, 1959 , vol. 1, p. 281,284
Yield: null

View all

8. Precursor and Product

precursor:

91335-13-6

56924-11-9

150717-69-4

462-06-6

103-84-4

93639-12-4

product :

459-57-4

403-42-9

61668-02-8

108-90-7

9. Other Information

9.0 Merck: 14,4598

9.1 Description: Haloperidol is a butyrophenone with a long duration of action. It has lile α- adrenoceptor blocking activity and minimal effect on the cardiovascular system. It is an effective antiemetic but has a high incidence of extrapyramidal adverse effects. Haloperidol may be used in the short-term management of the acutely agitated patient (when sinister causes of confusion such as hypoxaemia and sepsis have been excluded) and in the management of delirium in ICU. The duration of action of haloperidol is approximately 24–48h.

9.2 Chemical Properties: White Crystalline Powder

9.3 Originator: Haldol,Janssen-Le Brun,France,1960

9.4 Uses: Haloperidol is one of the most actively used modern neuroleptics. Its high antipsychotic activity is combined with a moderate sedative effect. It effectively stops various types of psychomotor excitement. It is used for schizophrenic psychoses, manic, paranoid, and delirious conditions, depression, psychomotor excitement of various origins, and for delirium and hallucinations of different origin.

9.5 Uses

Haloperidol has been used:

in ethanol to serves as an inhibitor of Erg2p
to address the mechanism of haloperidol in ferroptosis using hepatocellular carcinoma cells: Hep G2 and Huh-7 cell lines
in receptor internalization assay
as an antipsychotic drug in Dulbecco′s Modified Eagle medium

9.6 Usage: An antagonist for D2, D3, and D4 dopamine receptors that induces apoptosis of neurons in the striatum of rats

10. Computational chemical data

Molecular Weight: 375.868g/mol
Molecular Formula: C₂₁H₂₃ClFNO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 375.1401348
Monoisotopic Mass: 375.1401348
Complexity: 451
Rotatable Bond Count: 6
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 40.5
Heavy Atom Count: 26
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB6MQAEAAAAAAAAAAAAAAAAAAAAAAA8YIAAAAAAAAABQAAAHwIACAAADEbBmCwwAIMAAgCIAqBSAAACAAAkBQAIiAEICsgIJjKBlxCEcQAmwAGImYecyOCOhAAAAAAAAAAIAAAAAAAAAAAAAAAAAA==

11. Question & Answer

Synthesis of Haloperidol with 4-chlorobutanoyl chloride and piperidin-4-one Jun 08 2021
I searched for a easy synthesis on Haloperidol. Step 1 and 2 are taken from https://www.slideshare.net/SagarJoshi2/antipsychotics-33785528 (Slide 23). I just tried to work out a way to prepare 4-(4-chlorophenyl)piperidin-4-ol via Grignard. Does the 4-chloro group has any negative influence on the r...

13. Realated Product Infomation

3109-12-4 Dechloro Haloperidol (Haloperidol Impurity B)

72298-55-6 -Haloperidol|(d(4))-Haloperidol

72314-42-2 -Haloperidol|(d(8))-Haloperidol

1189986-59-1 Haloperidol-d4

1134807-34-3 Haloperidol Octanoate

65135-24-2 Haloperidol Lauroate

136765-35-0 HALOPERIDOL-D4

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